Parking management has attracted attention as an effective transportation policy. Although many studies analyzing parking lot choice behaviors have been conducted, most of them utilized data gathered by one-shot questionnaire surveys. Currently, in Japan, it is possible to easily observe parking lot choice behaviors over long time periods since online parking accounting machines have been introduced at many parking lots. In order to analyze and model the parking lot choice behaviors, we utilized massive parking accounting data including membership identification data. From the results of a basic analysis targeted at nine parking lots in Nagoya, we found that users rationally chose different parking lots according to their parking time, and some high-frequency users preferred to choose the same parking lot, indicating a similarity to habitual behavior. Moreover, we compared the characteristics of parking lot choice behaviors between high-frequency users and others by developing a parking lot choice model.